


What Happens In Cabo

by southsidestyle



Series: riverdale bingo: summer 2020 [7]
Category: Riverdale (TV 2017)
Genre: Barebacking, Beach Sex, Creampie, F/M, Hand Jobs, Infidelity, Public Sex, Revenge Sex, Riding
Language: English
Status: Completed
Published: 2020-11-05
Updated: 2020-11-05
Packaged: 2021-03-08 19:47:34
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,905
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27392197
Author URL: https://archiveofourown.org/users/southsidestyle/pseuds/southsidestyle
Summary: “I take it Toni’s not with you this week?”Jughead half expects Cheryl to snap at him for being nosy, but instead she just sighs and shakes her head. “We were originally booked to go on a short cruise for spring break.”“Yet you’re here,” Jughead points out. "With me."“Don’t remind me,” Cheryl groans, dragging her manicured nail along the edge of her phone case absently after Toni stops responding.
Relationships: Cheryl Blossom/Jughead Jones
Series: riverdale bingo: summer 2020 [7]
Series URL: https://archiveofourown.org/series/1902469
Comments: 7
Kudos: 69
Collections: Riverdale Bingo Summer 2020, Riverdale Kink Week





	What Happens In Cabo

**Author's Note:**

> One more for you guys, this time featuring my most requested pairing. I always get people asking me to write more of this pairing, so I knew I needed to use them for at least one of my bingo squares, and it might end up being my last. I wanted to get at least one line completed, and with this fic, I have officially done that, so yay! I only need one more to complete a second line, so there might be one more coming before the cut off, but I can't say that for sure yet, as I'm getting busy again. 
> 
> But I hope you guys enjoy this one, especially all the people that wanted more Cheryl/Jughead. This one doesn't have as much or as explicit smut as usual or my past fics for them, but hopefully you still like it. 
> 
> -
> 
> [Riverdale Bingo, Summer 2020](https://southsidestyle.tumblr.com/bingo): Spring Break.  
> [Riverdale Kink Week 2020](https://southsidestyle.tumblr.com/bingo): Choose Your Own Kinkventure.

Fun was the last thing Jughead Jones expected to have when he was dragged along to Cabo for spring break, but it turns out, that’s just what he ended up having. 

Well, actually, hanging out with _Cheryl Blossom_ was probably even further down on the list than fun, and he ended up doing that too. 

But the wildest part? 

It was hanging out with Cheryl Blossom that actually ended up being the fun part. 

He tries to tell himself it had more to do with the sex they had than the company, though.

\---

Jughead had originally planned on going back to Riverdale for the week to see his dad and get some work done, but when FP and Alice ended up taking a last minute trip to New York after Jellybean made her own plans with her friends, he didn’t see the point. 

So he figured he’d just stay in his dorm and enjoy the mostly abandoned campus instead. But then his roommate found out about his plans to be a hermit and he basically forced him along on his Cabo trip and now here he is.

In the blistering hot sun, surrounded by swarms of drunken idiots running around the hotel pool, or throwing each in it, or making out on the edge of it, or whatever else it is drunken idiots do on spring break.

The point is, Jughead might have had his arm twisted into coming here, but he’s not participating and he’s not having fun. 

What he _is_ doing is hiding out in the shade as far away from the pool as possible without actually being inside, wearing his beanie, denim shorts and a white wife beater, with his head in a book he’s already read at least five times before.

So basically, he may as well be back in Riverdale. 

If he just tries to zone out all the annoying noise, it’s almost bearable. Or it was, until—

“Hobo Caulfield?” Jughead hears from a few feet away, and even though he recognizes the voice immediately—and would obviously know who it was even if he didn’t, nobody else in the world is crass enough to call him that—he silently hopes he’s wrong. 

But when he reluctantly looks up from his book, he’s greeted with the sight of the Antichrist herself standing in front of him, familiar fiery red hair and pale skin on full display.

“Cheryl Blossom,” Jughead sighs as he closes his book. There’s no way he’s getting any more reading done now. “You're the last person I expected to run into this week.”

Despite his displeasure at her sudden appearance, he tries to keep his tone relatively neutral, because he enjoys being the bigger person by letting Cheryl make it snarky first, which she always does.

“I could say the same thing,” she responds dryly, taking off her sunglasses that are two times too big for her face. “You hardly strike me as the spring break type.”

“Was just thinking that about you,” Jughead shoots back truthfully, eyeing her half covered up bathing suit—she’s obviously not interested in the pool either. “I mean, don't people usually come on these trips with friends?” 

Well, so much for being the bigger person.

“Funny, Jones,” the redhead quips, but of course without a trace of amusement. She makes a show of glancing around him before retorting, “I don't see _your_ chums anywhere around here. Are they worried they may burst into flames if they come out in the sun?”

Jughead smirks, eyeing her ghostly white complexion. “Aren't you?”

She doesn’t have a witty comeback for that one. “So I see you’re just as insufferable as ever,” Cheryl huffs, tossing her hair over her shoulder as she crosses her arms. 

Jughead snorts, thinking this might be the closest they’ve ever been to being on the same wavelength. “Not to sound like a broken record, but right back at you.”

They haven’t seen each other since graduation, when everyone in the group of friends—if you could eve call them that—went their separate ways after everything blew up with Betty and Archie. He highly doubts he would have kept in touch with Cheryl at all even _if_ things between everyone ended on better terms, but if he was still with Betty, he figures he’d probably have _some_ knowledge of what the redhead has been up to over the last year, even if it was information he learned against his will.

As is, all he knows of the girl is that she had planned to go to High Smith College with Toni, and as far as he knows, she did. Though he doesn’t see a short pink haired girl anywhere around… 

But before he can ask her about it—in hopes of maybe finding someone he can actually stand to spend time with around here—someone is calling Cheryl’s name and pulling her attention away from him.

“Well, that’s my cue,” she mutters, not looking all that thrilled to go join who Jughead assumes are her friends—or whatever passes as friends to Cheryl. “As unpleasant as always, Forsythe.”

Jughead bites back a laugh at the look she shoots at him, but only gives her a two finger salute as she stalks away, saving his breath.

He watches her walk away for a moment before he shakes his head, not quite believing that actually just happened. Well, at least this vacation can surely only go up from here.

\---

But Jughead runs into Cheryl again the next day; ironically, in the elevator on the way down to the lobby.

“You again?” she sneers tiredly when the doors open and reveal him leaning against a corner of the suddenly much too small box. 

Jughead decides to go for chipper to piss her off even more. “Must be fate,” he smiles, watching as she checks to make sure the button for the lobby is lit up as the doors slide close.

“Fate _has_ always been quite cruel to me,” she responds, staying a few feet in front of him and not bothering to look back as she speaks. But considering all three walls are largely made up of mirrors, he can still see her face from his spot behind her.

“Is that why you’re vacationing alone?”

“I’m here with my sorority sisters, I’ll have you know,” Cheryl informs him, and he snorts at the predictably because of course she’s in a sorority. “And yourself?” she asks, clearly in the hopes of one upping him and not out of actual curiosity.

“My roommate and his friends,” Jughead is happy to share, though he does follow it up with a bit of honesty. “Though I was more dragged here than anything.”

Cheryl huffs in agreement. “It was hardly my first choice in spring break destinations either,” she tells him, but before she can elaborate—if she was even going to—the elevator dings, signalling their arrival in the lobby. 

When the doors slide open, a group of four girls is waiting nearby, and Jughead knows before they even say anything that they must be Cheryl’s friends. 

“There you are!” one of them calls out, waving Cheryl over impatiently. “You’re late.”

Jughead almost laughs at the demand and the way Cheryl promptly reacts to it, finding it more than a little amusing to witness the bossy redhead on the other side of power.

Cheryl throws a glance back at Jughead before she dutifully exits the elevator and heads towards them, as if telling him goodbye without actually saying anything.

And as he follows her out and moves in the opposite direction, he’s just able to hear, “Is that the hottie from yesterday? So you _do_ know him?” before he’s blissfully out of hearing range.

\---

Jughead doesn’t see Cheryl until the next day. Or rather, the next night—this time with their friends actually present.

He gets tricked into going to a karaoke bar, under the pretense that it’s just a regular bar, and after listening to drunk college kids butcher modern classics for two hours, Cheryl’s annoying voice is almost a relief.

“Do my eyes deceive me?” she sing-songs as she sidles up to Jughead at the bar. “Is Jughead Jones really out socializing?”

“Hello again, Cheryl,” he greets her, and he finds that after a long night, he doesn’t have the energy to feign displeasure at her present. After the last two run-ins, and knowing they’re in the same hotel for the next few days, seeing her is just an expected annoyance at this point, and not even the worst one he’s currently dealing with. “Are you going to grace us with a stirring rendition of a Riverdale High musical classic? I heard your totally appropriate performance of Sugar Daddy for our principal was a real crowd pleaser.”

She rolls her eyes as she waves down the bartender. “No songs for moi tonight,” she answers with an exaggerated pout. “But maybe you can treat the patrons of this fine establishment to a performance of your own. Maybe Origin of—”

“ _Cheryl_ ,” Jughead warns, his limited patience for her quickly running thin.

The redhead must sense how serious he is, because she backs off the topic and turns her attention to the bartender who asks for her order. She’s clearly ordering for her whole table, and Jughead could just leave in the amount of time it takes her to remember it all, but for some reason he doesn’t. 

Instead, he stays leaning on the bar even after she’s done, as if keeping her company while she waits for her order. 

Neither of them say anything, and instead stand watching the trio of girls on stage attempting to belt out a Whitney Houston cover— _attempting_ being the key word—until Cheryl’s phone pings and Jughead’s eyes curiously move down to her screen just in time to see her receive a message from Toni.

He doesn’t read their exchange, but whatever it is, it’s short, and he uses it as an opportunity to ask about the other girl. “I take it Toni’s not with you this week?”

Jughead half expects Cheryl to snap at him for being nosy, but instead she just sighs and shakes her head. “We were originally booked to go on a short cruise for spring break,” she explains, presumably the first choice destination she’d mentioned the day before. 

“Yet you’re here,” Jughead points out. “With me.”

“Don’t remind me,” Cheryl groans, dragging her manicured nail along the edge of her phone case absently after Toni stops responding. “Sweet Pea called her up last minute and invited her on a road trip to Pittsburgh to visit the third stooge, and that was apparently more appealing to her than a week with me in a bikini on a boat.”

The beanie-wearing boy cringes at Toni’s choice, both understanding not wanting to be trapped with Cheryl at sea and knowing that’s not a good look for a girlfriend. He can only assume things between them aren’t great at the moment if she’s pulling things like that, but he doesn’t dare to ask. 

“My dad ditched our spring break plans too,” he says instead, just as the bartender returns with her order, even though he knows it’s not the same thing.

Cheryl hums, reaching for one of the newly arrived shot glasses and raises it in Jughead’s direction before downing it and then carefully picking up the rest of the tray of drinks. 

“Until tomorrow, I’m sure,” she says as she makes her exit, and Jughead definitely doesn’t watch her walk away this time.

\---

Just as Cheryl predicted and Jughead has come to expect, they do see each other the next day.

It turns out, one of her sorority sisters—the one she’s rooming with on their trip, even—met Jughead’s roommate at the bar last night and they really hit it off and made plans to go to dinner tonight. For the four of them. 

Well, they made tentative plans to go on a date, but it has since evolved into a dinner between them and a wing man and woman of their choice, and naturally, Jughead gets roped into being that wing man. And even though he doesn’t know for sure that Cheryl is going to be the wing woman, why would he think it would be anyone else at this point?

And of course he’s right. 

Judging by the complete nonreaction his presence garners from Cheryl when they first spot each other, she must have predicted this as well. Which begs the question: why did she still come then? But then again, why did _he_? 

Not wanting to give it much thought, Jughead tries to push those questions to the back of his mind for the night, which doesn’t prove to be too difficult, considering they’re at a buffet and his friend is paying, so he actually manages to enjoy himself for a couple hours on this trip.

Or he does, until he comes back from his third trip to the buffet to find Cheryl is the only one still sitting at their table. 

“Where’d they go?”

“Back to our room,” she answers dryly, pushing what’s left of her food around her plate dejectedly. “Which means I’m stuck here with you for at least an hour.”

Jughead snorts as he takes his seat across from her at the table. “I live with the guy, and trust me, an hour is being very generous.” It surprisingly gets a small smile out of Cheryl, which Jughead finds himself weirdly proud of, but it’s falling from her face all too soon when her phone lights up with a new text message. “Everything okay?”

“It’s just Toni,” Cheryl sighs without a trace of that sickly sweet, loving tone she always used to have when speaking of her girlfriend. “She can’t FaceTime tonight like we’d planned.”

“That sucks,” he commiserates as he bites into a wing, taking a moment to consider if he wants to brave this conversation or not. Eventually he decides that it’s better than sitting in awkward silence. “I take it things aren’t all good with you guys?”

And to his surprise, as if she was just waiting for someone— _anyone_ —to ask her, Cheryl immediately starts spilling her guts out to him. 

She tells him all about how good things were for most of their first semester at High Smith, but how off they’ve been since going back to school after Christmas break; Toni’s working full time at the newspaper and joined a few other clubs, while a lot of Cheryl’s time has been spent at the sorority house now that she’s no longer a pledge. 

Apparently after living together for half of high school, they decided to room separately for their first year at college, and now that decision is biting them in the ass, because they don’t even get to go home to each other at the end of the day anymore. They don’t even see each other some days, and for a couple he remembers as being attached at the hip, he’s not surprised that’s created such a rift between them. 

Spring break was supposed to be their chance to reconnect, but Toni bailed and now Cheryl’s convinced they’re not even going to last until the summer, and she’s probably right. 

Jughead doesn’t really know what advice to offer her, considering the state of his own love life and how horrible his one serious relationship ended last year, but he does listen to her at least, and that seems to be good enough for her. 

It’s probably the most human Jughead has ever seen Cheryl, at least in a one-on-one sense, and though it doesn’t erase her behavior from the previous fifteen or so years he’s known her, it does give him a new perspective of her.

They don’t part with a hug or anything overly friendly like that, but she does thank him for listening as they’re leaving, and even uses his preferred name too. 

\---

“Sorry for ditching you after dragging you out, man,” his roommate apologizes to him when he gets back to their hotel room later that night, even though Jughead doubts he’s all that sorry. 

“It’s okay,” he says anyways from his bed, his computer open on his lap. “I ended up having a good time.”

His roommate grins as he drops down on his own bed. “I bet you did,” he laughs. “She was hot as fuck. They definitely didn’t have girls like that at my high school.”

“It’s not like that,” Jughead insists, thrown by the mere implication. “We just talked. She has a girlfriend.”

“Hey, what happens in Cabo, stays in Cabo,” the other guy shrugs, pulling out his suitcase from underneath his bed as he launches into oversharing the details of his night.

Jughead just rolls his eyes and tunes him out, suddenly missing Cheryl’s company.

\---

  
  
He almost lives to regret that thought when he finds out their mutual friends have made plans for both of their entire groups to spend their last full vacation day together on the beach, but Cheryl proves to be human two days in a row, so it’s not too bad. 

It’s actually kind of nice to have someone to sulk with on the sidelines for once, watching while their friends play volleyball, wander into the ocean and get progressively more drunk as the day wears on.

Jughead would’ve been fine on his own, but nobody bothers him about being a joiner when she’s sitting beside him, and it gives him a chance to hear about what people from high school are up to, from someone that actually talks to them and doesn’t just absentmindedly like a picture on occasion. 

Cheryl seems to make a point to avoid any mention of Betty or Archie, which Jughead is grateful for, but after a while, he can’t resist bringing them up himself.

“Nobody’s really heard from Archie,” she admits dejectedly, clearly worried about her fellow ginger; they were never that close, but Jughead thinks a part of Cheryl has been seeing a bit of Jason in him since her brother’s death, so he’ll always have a special place in her heart. 

Jughead is a little worried himself, knowing Archie has a penchant for getting himself into trouble without even trying, but there’s nothing he can do about it, so he tries to push those thoughts to the back of his head and remember why he doesn’t like to think of the other boy at all these days.

Which brings him to his next question: “And Betty?”

Cheryl looks hesitant to answer, but eventually shrugs. “Last I heard, she was doing well,” she confirms, keeping her tone light. “We talked last month and she sounded in high spirits. The work is hard, of course—isn’t it for us all?—but she seemed to be in her element.”

It’s surprisingly good to hear, Jughead finds. He still cares about the girl and knows she didn’t mean to hurt him, but some things he just can’t get passed, so this is where they are now—getting life updates through Cheryl Blossom.

He doesn’t hate her though and wishes her well, so he’s happy for her. 

“Good for her,” is all he can muster up to say, because he worries if he says anything more, he’ll ask if she’s seeing someone new, and that’s something he definitely doesn’t care to know.

\---

After ordering an insane amount of pizza, even by Jughead’s standards, and watching the sun go down, the group unfortunately elects to stay on the beach for the night and have a bonfire in the fire pit that’s just a little ways away from where they’ve spent the day.

Jughead realizes that he could probably get away with sneaking off back to his room without much judgment now, but for some reason, when he sees Cheryl plans on staying put, he decides to as well.

But he lives to regret that decision when he makes the mistake of checking his Instagram while Cheryl is beside him, and accidentally plays a story meant for Fangs’ Close Friends list, that features him drunkenly narrating the scene he’s filming: Toni draping herself all over Sweet Pea while they’re dancing at a nightclub, that abruptly ends with the boy cackling as he swiftly averts the camera just as Toni is pulling Sweet Pea in for a sloppy kiss.

Cheryl isn’t close enough to see it the first time, but Fangs’ obnoxious commentary is heard loud and clear, and leaves little to the imagination, so there’s nothing Jughead can do when she insists on making him play it back for her to watch.

“I’m sure it didn’t mean anything,” Jughead tries to assure her while she stares blankly at his phone screen, long after it’s moved onto other stories, even though he knows that wouldn't have changed anything for him, back when he was in her shoes. “They’re probably both as drunk as Fangs is.”

But Cheryl’s not interested in his platitudes or excuses, or in talking about it at all, it seems, because after she stews silently for a good five minutes after watching her girlfriend cheat on her, she abruptly stands up and asks Jughead if he wants to go for a walk with her. 

And even though he’s kind of tired and it’s kind of cold out at this hour—they’re both in bathing suits, despite not even going near the water—he can’t seem to deny her.

\---

Jughead realizes soon enough—as Cheryl’s soft lips suck his between her own and her hand slips into his swimming trunks—that he really should have known what she had in mind when she invited him to go on a _walk_ , but it’s not like he has a lot of experience with girls.

He hasn’t been with anyone since his break up with Betty, so the only other girl on his list is, ironically, the girl whose infidelity triggered this.

So as naive as it may be, Jughead was surprised when Cheryl pulled him behind a group of giant rocks sitting on the beach after only a few minutes of walking, and kissed him.

“Whoa, whoa, Cheryl, wait,” he’d protested, gently pushing her off of him after finally registering what was happening. “What are you doing?”

“I’m _trying_ to fuck you,” she had answered bluntly, her eyes full and dark in the moonlight. “Don’t even try to tell me you don’t want me. I’ve seen the way you’ve been looking at me all week.”

And as much as Jughead wished he could deny it, he couldn’t.

Cheryl had always been hot, but somehow she just got hotter in college, and now that his tolerance for her had improved, he’d gone from just being able to appreciate her attractiveness to being outright attracted _to_ her, even if he’d only realized it just then.

But still, hot or not, she had a girlfriend. 

A girlfriend that was also his friend, though they hadn’t spoken since graduation. And after what he went through with Betty and Archie, could he really do that to someone else? Yes, Toni cheated first by kissing Sweet Pea and she could have very well be fucking him at that moment for all they knew, but it could’ve also just been one drunken mistake that she immediately regretted and planned to tell Cheryl about the next time they talked.

But above all the thoughts and reasonings that were running through his mind, his roommate’s voice cut through it all: what happens in Cabo, stays in Cabo.

So, _fuck it_ , he decides.

“Are you sure?” he checked with her once he made up his mind, though it still felt like a question better asked of himself. 

But Cheryl seemed to have a lot less reservations about cheating on Toni than Jughead did, because instead of answering him, she’d simply slipped her hand into his shorts and wrapped her nimble fingers around his cock as she kissed him again.

And who was Jughead to disagree with an argument like that? 

So he doesn’t. 

Instead, he just kisses Cheryl back and lets her work his cock to full length with an expertise he didn’t think she’d possess, considering the equipment she’s used to working with.

He’s ready to go in what might be record time, and offers no protest when she moves him over to a different, lower rock, so that when she pushes him back, he’s leaning against it at enough of an angle for her to climb on top of him. 

“We don’t have a condom,” Jughead barely has enough presence of mind to point out as Cheryl fishes his hard cock out of his shorts with one hand and moves her bathing suit out of the way with her other, before guiding his head through her already wet folds. 

“Does it look like I give a fuck, Jughead?” she snaps back at him, rolling her eyes in annoyance and then pleasure as she sinks down on his dick as soon as the words leave her lips. “Oh _fuck_.”

Jughead has to wonder if she’s ever had a real cock inside of her before—he seems to remember rumors of her and Chuck Clayton in freshman year, and of course those much crazier ones about her and Jason, but as far as he knows, they’ve always only just been that, rumors. 

Toni is the only person he knows of her being with, and something about the thought of being the first—and probably _only_ —guy Cheryl has or ever will fuck, is thrilling. Not to mention a huge self esteem booster.

He knows it’s just because he happened to be there with her when she saw that video of Toni, but he doesn’t care; there was a beach full of both girls and guys she could have grabbed for a quick revenge fuck, but she chose _him_.

So as Cheryl starts to rock her hips and ride his cock, Jughead decides he’s going to make sure he makes it as good for her as possible.

He focuses on her clit, nudging her bathing suit bottoms further to the side so he can rub tight circles against it with his thumb while she bounces on top of him.

There’s not much else he can do for her in this position, but it’s obvious that she’s craving control right now, so as tempted as Jughead is to flip them over and give Cheryl a nice thorough fucking, he’s not sure that’s what she wants, let alone needs.

So instead, he just sits up and wraps his other arm around the small of her back to keep her in his lap, and starts mirroring her rocking, meeting her half way.

It’s not the most graceful sex he’s ever had, and the angle of his arm between them is a little awkward, but it seems to be working for the both of them anyways, and that’s what matters. 

Jughead hisses as Cheryl’s sharp nails dig into his shoulder as she holds onto him tightly, but that quickly dissolves into moans when she picks up her pace a bit.

They’re not that far away from their friends though, so when Jughead fears he might get a little too loud, he buries his face in the ample cleavage that’s bouncing in front of—something he must admit he always wanted to do whenever Cheryl walked around school with her tits falling out of her top, which was a lot.

It’s not long before Jughead feels his balls tightening, and he’d be embarrassed by his stamina if Cheryl’s wildly bucking hips weren’t hinting at the fact that she’s just as close. 

With just the right amount of teamwork, they manage to come together soon after; Cheryl mewls as her cunt squeezes Jughead’s cock tightly as it starts to spurt ropes of warm cum deep inside of her, the both of them clinging to each other as they come undone. 

They stay tangled together as they come down, panting into the cold night air as their bodies buzz with leftover endorphins. 

Jughead expects Cheryl to freak out after the moment passes, but to his surprise, when she pulls away, it’s only to press a kiss to his lips before she moves to his ear and invites him back to her room for another couple of rounds. 

Of course he says yes.

\---

Luckily for both of them, Cheryl’s roommate doesn’t mind sleeping in Jughead’s room with his friend after they come back to the hotel later and find a sock on their door knob, leaving the two of them with the room to themselves for the rest of the night to make good use of.

And that’s exactly what they do—in the both beds, on the couch, against the window, on the balcony, the bathroom counter top and even the shower. 

It’s pretty much the best night of Jughead’s life, and the perfect way to end this trip that turned out to be way better than he ever expected it to be. 

They don’t talk about Toni at all—Betty or Archie either—and they don’t talk about what comes after this, when they both go back to school and back to ignoring the others' existence. 

Cheryl and Jughead just enjoy each other and make sure to make every last minute of what’s left of their spring break count.

**Author's Note:**

> Would very much appreciate it if you hit that kudos button or left a comment if you liked it. Thanks for reading!


End file.
